Table 1 HR-MS data for primaquine and its metabolites from human plasma and urine samples
# | RT (min) | Exact mass | Peaka [M + H]+ | Molecular Formula | Biotransformation (Metabolite Predicted/Identified) | Sample/source |
|---|---|---|---|---|---|---|
1 | 3.5 | 273.1477 | 274.1549 (274.1550) | C15H19N3O2 | Hydroxylation and quinone-imine formation | Plasma/urine |
2 | 4.97 | 259.1679 | 260.1769 (260.1757) | C15H21N3O | Precursor ion (PQ) | |
3 | 5.3 | 256.1206 | 257.1273 (257.1285) | C15H16N2O2 | Oxidative deamination to acid + cyclization (Carboxyprimaquine lactam) | |
4 | 7.98 | 479.1898 | 480.1992 (480.1977) | C22H29N3O9 | Carbamoyl glucuronide formation (PQ-N-carbamoyl-glucuronide conjugate) | |
5 | 8.95 | 274.1312 | 275.1385 (275.1390) | C15H18N2O3 | Deamination + Acid (Carboxyprimaquine) | |
6 | 10.12 | 288.1468 | 289.1560 (289.1547) | C16H20N2O3 | Deamination + Acid + Methylation (Carboxyprimaquine methyl ester) | |
7 | 4.67 | 421.2207 | 422.2315 (422.2286) | C21H31N3O6 | Glucose conjugation | Plasma |
8 | 6.03 | 320.1367 | 321.1454 (321.1445) | C16H20N2O5 | (Deamindation + acid) + 2xOH + methylation (dihydroxy carboxyprimaquine methyl ester) | |
9 | 9.65 | 317.1734 | 318.1789 (318.1812) | C17H23N3O3 | Methyl carbamate formation (PQ methyl carbamate) | |
10 | 1.78 | 259.1315 | 260.1403 (260.1399)* | C14H17N3O2 | 5-Hydroxylation +Orthoquinone formation (5,6 orthoquinone primaquine) | Urine |
11 | 1.9 | 451.1955 | 452.2011 (452.2027) | C21H29N3O8 | Hydroxylation + Glucuronide conjugation | |
12 | 2.2 | 421.1849 | 422.1908 (422.1922) | C20H27N3O7 | 5-Demethylation + Glucuronidation (5-desmethyl PQ glucuronide) | |
13 | 2.32 | 451.1955 | 452.2011 (452.2027) | C21H29N3O8 | Hydroxylation + Glucuronide conjugation | |
14 | 2.34 | 275.1634 | 276.1712 (276.1707) | C15H21N3O2 | Hydroxylation (4-OH PQ) | |
15 | 3.1 | 452.1795 | 453.1881 (453.1868) | C21H28N2O9 | Deamination + alcohol + hydroxylation + glucuronidation | |
16 | 3.12 | 315.1947 | 316.2002 (316.2020) | C18H25N3O2 | Methylation + Acetylation | |
17 | 3.45 | 275.1634 | 276.1694 (276.1707) | C15H21N3O2 | Hydroxylation | |
18 | 3.85 | 275.1634 | 276.1697 (276.1707) | C15H21N3O2 | Hydroxylation (2-OH PQ) | |
19 | 4.43 | 245.1528 | 246.1617 (246.1601) | C14H19N3O | Demethylation | |
20 | 4.88 | 493.206 | 494.2127 (494.2133) | C23H31N3O9 | Acetylation + (Hydroxylation + Glucuronide conjugation) | |
21 | 4.92 | 275.1634 | 276.1705 (276.1707) | C15H21N3O2 | Hydroxylation (3-OH PQ) | |
22 | 5.18 | 273.1477 | 274.1534 (274.1550) | C15H19N3O2 | Hydroxylation and quinone-imine formation | |
23 | 5.67 | 483.1853 | 484.1932 (484.1926) | C21H29N3O10 | 3 x Hydroxylation + 1 x glucuronide conjugation | |
24 | 5.9 | 289.1426 | 290.1500 (290.1499) | C15H19N3O3 | 2 x Hydroxylation + quinone-imine formation | |
25 | 5.92 | 291.1583 | 292.1647 (292.1656) | C15H21N3O3 | 2 x hydroxylation | |
26 | 6.15 | 498.1486 | 499.1545 (499.1559) | C21H26N2O12 | Deamination + acid + 3 x hydroxylation + 1 x glucuronide conjugate | |
27 | 6.17 | 466.1587 | 467.1666 (467.1660) | C21H26N2O10 | (Hydroxylation + glucuronide conjugation) + (deamination + acid) | |
28 | 6.4 | 291.1583 | 292.1647 (292.1656) | C15H21N3O3 | 2 x hydroxylation | |
29 | 7.27 | 301.179 | 302.1875 (302.1863) | C17H23N3O2 | Acetylation | |
30 | 7.6 | 435.2006 | 436.2100 (436.2078) | C21H29N3O7 | Glucuronide conjugation | |
31 | 7.74 | 436.1846 | 437.1909 (437.1918) | C21H28N2O8 | Oxidative deamination to alcohol + glucuronide conjugation | |
32 | 7.79 | 450.1638 | 451.1714 (451.1711) | C21H26N2O9 | (Deamination + acid) + glucuronide conjugation | |
33 | 8.2 | 276.1474 | 277.1552 (277.1547) | C15H20N2O3 | Deamination + alcohol + hydroxylation | |
34 | 8.6 | 435.2006 | 436.2100 (436.2078) | C21H29N3O7 | Glucuronide conjugation | |
35 | 8.65 | 315.1583 | 316.1676 (316.1656) | C17H21N3O3 | Acetylation + hydroxylation + quinone-imine formation | |
36 | 10.38 | 302.1267 | 303.1324 (303.1339) | C16H18N2O4 | Deamination + acid + methylation + hydroxylation + quinone-imine formation |